Tertiary alkanolamines containing surface active alkyl groups

ABSTRACT

The present invention relates to novel tertiary alkanolamines useful as catalysts for preparing polyurethane foams and as additives to reduce the dynamic surface tension of aqueous solutions. The tertiary alkanolamines may be represented by formula (I):                  
 
wherein A, R 1 –R 6 , and n are defined herein.

FIELD OF THE INVENTION

The present invention relates to the use of novel tertiary alkanolaminesprepared by reacting a terminal epoxy compound with a primary orsecondary amine. The new tertiary alkanolamines are useful as catalystsfor preparing polyurethane foams and as additives to reduce the dynamicsurface tension of aqueous solutions.

BACKGROUND OF THE INVENTION

Polyurethane foams are widely known and used in automotive, housing, andother industries. Polyurethane foams are prepared by reacting apolyisocyanate with a polyol in the presence of various additives. Onesuch additive is a chlorofluorocarbon (CFC) blowing agent, whichvaporizes as a result of the reaction exotherm, which causes thepolymerizing mass to form a foam. The discovery that chlorofluorocarbonsdeplete ozone in the stratosphere has resulted in mandates lowering theuse of chlorofluorocarbons. The use of water blown foams, in whichblowing function is performed by CO₂ generated from the reaction ofwater with a polyisocyanate, has therefore become increasinglyimportant. Tertiary amine catalysts are often used to accelerate theblowing (reaction of water with a polyisocyanate) and gelling (reactionof a polyol with an isocyanate) functions.

The ability of the tertiary amine catalyst to selectively promote eitherblowing or gelling is an important consideration in selecting a catalystfor preparing a particular polyurethane foam. If a catalyst promotes theblowing reaction too quickly, a substantial portion of the CO₂ will beevolved and will bubble out of the formulation before sufficientreaction of the isocyanate with the polyol has occurred, resulting incollapse of the foam and the production of a poor quality foam. On theother hand, if a catalyst promotes the gelling reaction too quickly, asubstantial portion of the polymerization will have occurred beforesufficient CO₂ has been evolved, resulting in insufficient blowingaction and the production of a poor quality foam.

Tertiary amine catalysts are generally malodorous and offensive and manyare highly volatile due to their low molecular weight. The release oftertiary amine during foam processing may present significant safety andtoxicity problems and the release of residual amine during customerhandling is undesirable. On the other hand, low vapor pressure-highmolecular weight amine catalysts are expected to require very highcatalyst usage due to their low N/C ratio making the manufacturing costvery high.

Surprisingly, amine catalysts which contain hydroxyl groups as well ashigher-alkyl (C₆ or higher) or fatty acid groups have shown an unusualhigh activity making their usage level relatively modest. Their highmolecular weight, reduced volatility and odor can limit the exposure ofoperators to offensive amine vapors. Furthermore, catalysts whichcontain hydroxyl functionality can chemically bind into the urethaneduring the reaction and are not released from the finished product.Catalysts of this type are typically of low to moderate activity andpromote both the blowing (water-isocyanate) and the gelling(polyol-isocyanate) reactions to varying extents.

U.S. Pat. No. 4,148,762 discloses the use of the product obtained fromreacting N,N-dimethyl-1,3-propanediamine with a C₁–C₁₈ non-terminal andnon-glycidyl epoxy mixture in glycerol to give the aminoalkanol that wasfurther treated with sodium chloroacetate to give a betaine said to beuseful in cosmetic applications.

U.S. Pat. No. 4,644,017 discloses diffusion stable amino alkyl ureashaving tertiary amino groups said to be useful during the preparation ofa polyisocyanate addition product which do not discolor or change theconstitution of surrounding materials. Specifically taught are CatalystA and Catalyst D which are reaction products ofdimethylamino-propylamine and urea.

U.S. Pat. No. 4,007,140 discloses the use ofN,N′-bis(3-dimethylaminopropyl)urea as a low odor catalyst for preparingpolyurethanes and the use of N-(3-dimethylaminopropyl)-formamide as acatalyst to make polyurethane foams.

U.S. Pat. No. 4,012,445 describes the use of beta-amino carbonylcompounds as catalysts for preparing polyurethane foams. The beta-aminopart of the catalyst is present as a dialkylamino or a N-morpholino or aN,N′-piperazino heterocyclic nucleus and the carbonyl part is present asan amido or ester.

U.S. Pat. No. 4,735,970 discloses a process for preparing cellularpolyurethanes using amine-CO₂ adducts, homogeneous mixtures of theseadducts, and the use of N-(3-dimethylaminopropyl)-formamide as catalyststo make polyurethane foams.

U.S. Pat. No. 5,200,434 describes the use of amide derivatives ofalkylene oxide polyethers and their uses in polyurethane foamformulation.

U.S. Pat. Nos. 5,302,303; 5,374,486 and 5,124,367 disclose that theshelf-life stability of isocyanate-reactive compositions is oftenadversely affected by the addition of flame-retardants, especially thosebased on phosphorous, zinc, antimony and aluminum, and that the use offatty amido-amines stabilizes isocyanate compositions containingflame-retardants.

U.S. Pat. No. 4,710,191 relates to the preparation of polyurethane foamsusing hydroxyl-quinuclidine derivatives such as 3-hydroxymethylquinuclidine, 3-methyl-3-hydroxymethyl quinuclidine, and 4-hydroxymethylquinuclidine.

U.S. Pat. Nos. 5,233,039; 5,194,609; 5,233,039 and 5,143,944 describe amethod for making polyurethane foams using 3-quinuclidinol and itsderivatives.

U.S. Pat. Nos. 5,559,161; 5,633,293 and 5,508,314 describe a method formaking a polyurethane foam using hydroxyl-containing tertiary amines asfoaming catalysts. The catalysts composition used were essentiallypermethylated mono- and/or dialkylene oxide adducts oftris(2-aminoethyl)amine.

U.S. Pat. No. 4,650,000 discloses adducts prepared by the reaction ofpolyamines with C6–C18 alkyl glycidyl ethers. The adducts are said to beeffective surfactants for the formation of microemulsions containing ahydrocarbon oil and aqueous solutions used to treat subterranean rockformations surrounding oil and gas wells. The amine surfactants wereutilized in the microemulsions as cationic quaternary ammonium salts.

U.S. Pat. No. 4,797,202 discloses N-(hydrocarbyl)-α,ω-alkanediamines ascollectors for the recovery of minerals from mineral ores by frothflotation. In particular, the 1:1 adduct of diethylenetriamine and2-ethylhexyl glycidyl ether was shown to be effective for copperrecovery in the froth flotation of copper sulfide.

CH 313,159 discloses a process for the preparation of stable dye andstripper baths containing positively charged amine additives. The bathscontain 1:1 adducts of diamines and polyamines and C8 and greateralkylglycidyl ethers and the corresponding alkylated amines are formedby subsequent reactions with ethylene oxide, dimethyl sulfate,chloroacetic acid and other reagents.

U.S. Pat. No. 4,311,618 discloses the use of a water soluble cleanserconcentrate comprising an ionic surfactant, a non-ionic surfactant, anamphoteric dissociating agent and an organic aprotic solvent. Example 5discloses the hydrochloride salt of the 1:2 adduct of diethylenetriamineand 2-ethylhexyl glycidyl ether.

JP52018047 discloses adducts prepared by the reaction of polyamines andup to 3 C6–C16 alkyl glycidyl ethers which are said to be useful asbactericides.

JP 450119973 discloses adducts prepared by the reaction of polyaminesand up to 3 C6–C16 alkyl glycidyl ethers which also contain carboxylategroups which are said to be useful as bactericidal surfactants.

U.S. Pat. No. 3,931,430 discloses the use of the products of diaminesand polyamines and C4–C16 glycidyl esters and ethers said to be usefulas desensitizers for pressure-sensitive recording sheets. Thesedesensitizers must be soluble in an oil vehicle used to make non-aqueousink for offset printing.

U.S. Pat. No. 6,437,185 discloses quaternary ammonium compounds preparedsalts from alkoxylated polycat 15 reacted with an alpha, beta epoxyalkane. The quaternization takes place with a product such as a diethylsulfate and the product is said to be useful as a conditioner of hair,fiber, and textile.

SUMMARY OF THE INVENTION

The present invention relates to novel tertiary alkanolamines useful ascatalysts for preparing polyurethane foams and as additives to reducethe dynamic surface tension of aqueous solutions. The tertiaryalkanolamines may be represented by formula (I):

wherein A represents CH or N;

-   R¹ represents hydrogen and R⁶ represents —CH₂C(R⁷)(OH)CH₂OR⁸; or-   R¹ represents-    and R⁶ represents —CH₂C(R⁷)(OH)CH₂OR⁸; or-   R¹ represents —CH₂C(R⁷)(OH)CH₂OR⁸ and R⁶ represents an alkyl or    alkenyl group having C₄–C₃₆ carbon atoms; or-   R¹ represents hydrogen and R⁶ represents —CH₂C(R⁷)(OH)R⁸; or-   R¹ represents-    and R⁶ represents —CH₂C(R⁷)(OH)R⁸; or-   R¹ represents —CH₂C(R⁷)(OH)R⁸ and R⁶ represents an alkyl or alkenyl    group having C₄–C₃₆ carbon atoms;-   R² and R³ each represent hydrogen or an alkyl or alkenyl group    having C₁–C₆ carbon atoms;-   R⁴ and R⁵ each represent an alkyl group having C₁–C₆ carbon atoms    when A represents N; or-   R⁴ and R⁵ together represent a C₂–C₅ alkylene group when A    represents N; or-   R⁴ and R⁵ together represent a C₂–C₅ alkylene group containing NR¹⁰    or NR¹¹ when A is CH or N, where R¹⁰ is hydrogen or an alkyl group    having C₁–C₄ carbon atoms and R¹¹ is an alkyl group having C₁–C₄    carbon atoms or-   R⁷ represents hydrogen or an alkyl or alkenyl group having C₁–C₅    carbon atoms;-   R⁸ represents an alkyl or alkenyl group having C₄–C₃₆ carbon atoms    or —COR⁹, where R⁹ represents an alkyl or alkenyl group having    C₃–C₃₅ carbon atoms; and-   n is an integer from 1 to 3.

When the tertiary alkanolamines of the invention are used as catalystsin polyurethane applications, the catalysts are typically used in thepresence of a gelling catalyst but combinations of blowing and gellingcatalysts are also possible. The reactive catalyst compositions containat least one hydroxyl group that enables the catalyst to react into thepolyurethane matrix thereby immobilizing the amine during and afterpolymerization. These reactive catalysts can be used as gellingcatalysts or blowing catalysts with the aid (or not) of complementarytertiary amine blowing or gelling co-catalysts, which may or may notcontain reactive functional groups to produce polyurethane foammaterials. The reactive catalysts have no amine emissions in thefinished product, have low vapor pressures and low odor, and have loweramine concentration and optimum kinetics and physical properties. Theappropriate selection of these reactive catalysts in conjunction (ornot) with complementary gelling or blowing amine co-catalysts canprovide foams with optimum airflows. Good airflow means improvedporosity and openness which is an indication of improved dimensionalstability of the foam. The surfactant properties of the tertiaryalkanolamines help in micronising and stabilizing the foam. While thetertiary alkanolamines act as defoaming surfactants in inks with waterbased systems, the tertiary alkanolamines will stabilize and promotefoam in polyurethane systems.

DETAILED DESCRIPTION OF THE INVENTION

The present invention relates to a compound represented by formula (I):

In formula (I), A represents CH or N.

-   R¹ may represent hydrogen and R⁶ may represent —CH₂C(R⁷)(OH)CH₂OR⁸;    or-   R¹ may represent-    and R⁶ may represent —CH₂C(R⁷)(OH)CH₂OR⁸; or-   R¹ may represent —CH₂C(R⁷)(OH)CH₂OR⁸ and R⁶ may represent an alkyl    or alkenyl group having C₄–C₃₆ carbon atoms; or-   R¹ may represent hydrogen and R⁶ may represent —CH₂C(R⁷)(OH)R⁸; or-   R¹ may represent-    and R⁶ may represent —CH₂C(R⁷)(OH)R⁸; or-   R¹ may represent —CH₂C(R⁷)(OH)R⁸ and R⁶ may represent an alkyl or    alkenyl group having C₄–C₃₆ carbon atoms;-   preferably R¹ is hydrogen or-   R² and R³ each represent hydrogen or an alkyl or alkenyl group    having C₁–C₆ carbon atoms; preferably R² and R³ are hydrogen;-   R⁴ and R⁵ may each represent an alkyl group having C₁–C₆ carbon    atoms when A represents N; or-   R⁴ and R⁵ together may represent a C₂–C₅ alkylene group when A    represents N; or-   R⁴ and R⁵ together may represent a C₂–C₅ alkylene group containing    NR¹⁰ or NR¹¹ when A is CH or N, where R¹⁰ is hydrogen or an alkyl    group having C₁–C₄ carbon atoms and R¹¹ is an alkyl group having    C₁–C₄ carbon atoms or-    preferably R⁴ and R⁵ are alkyl groups having C₁–C₆ carbon atoms    when A represents N;-   and preferably R⁴ and R⁵ together represent —CH₂CH₂N(CH₃)CH₂—;-   R⁷ represents hydrogen or an alkyl or alkenyl group having C₁–C₅    carbon atoms;-   preferably R⁷ represents hydrogen;-   R⁸ represents an alkyl or alkenyl group having C₄–C₃₆ carbon atoms    or —COR⁹;-   where R⁹ represents an alkyl or alkenyl group having C₃–C₃₅ carbon    atoms;-   preferably R⁸ represents an alkyl or alkenyl group having C₄–C₂₂    carbon atoms or —COR⁹;-   preferably R⁹ represents an alkyl or alkenyl group having C₃–C₂₂    carbon atoms;-   n is an integer from 1 to 3; preferably from 2 to 3.

The compounds and methods of the present invention are more fullydescribed in copending patent application entitled “TertiaryAlkanolamine Polyurethane Catalysts Derived From Long Chain Alkyl andFatty Carboxylic Acids”, filed by applicants concurrently with thepresent patent application and assigned to the assignee of thisapplication, which application is hereby incorporated by reference.

Preferably, the tertiary alkanolamine compound is selected from thegroup consisting ofN,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-octadecyl ether)amine, N-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-octadecyl ether)amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-hexadecylether) amine, N-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-hexadecylether) amine,N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-tetradecyl ether)amine, N-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-tetradecyl ether)amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-dodecyl ether)amine, N-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-dodecyl ether)amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-decyl ether)amine, N-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-decyl ether) amine,N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-octyl ether) amine,N-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-octyl ether) amine,N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-2-ethylhexyl ether)amine, N-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-2-ethylhexyl ether)amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-hexyl ether)amine, N-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-hexyl ether) amine,N,N-bis-(3-dimethylaminopropyl)-N-(2-hexanol) amine,N-(3-dimethylaminopropyl)-N-(2-hexanol) amine,N,N-bis-(3-dimethylaminopropyl)-N-(2-octanol) amine,N-(3-dimethylaminopropyl)-N-(2-octanol) amine,N,N-bis-(3-dimethylaminopropyl)-N-(2-decanol) amine,N-(3-dimethylaminopropyl)-N-(2-decanol) amine,N,N-bis-(3-dimethylaminopropyl)-N-(2-dodecanol) amine,N-(3-dimethylaminopropyl)-N-(2-dodecanol) amine,N,N-bis-(3-dimethylaminopropyl)-N-(2-tetradecanol) amine,N-(3-dimethylaminopropyl)-N-(2-tetradecanol) amine,N,N-bis-(3-dimethylaminopropyl)-N-(2-hexadecanol) amine,N-(3-dimethylaminopropyl)-N-(2-hexadecanol) amine,N,N-bis-(3-dimethylaminopropyl)-N-(2-octadecanol) amine,N-(3-dimethylaminopropyl)-N-(2-octadecanol) amine;N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl butyl ether) amine;and N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-neodecanoicester) amine.

More preferably the compound is selected from the group consisting ofN,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-octadecyl ether)amine, N-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-octadecyl ether)amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-hexadecylether) amine, N-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-hexadecylether) amine,N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-tetradecyl ether)amine, N-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-tetradecyl ether)amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-dodecyl ether)amine, N-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-dodecyl ether)amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-decyl ether)amine, N-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-decyl ether) amine,N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-octyl ether) amine,N-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-octyl ether) amine,N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-2-ethylhexyl ether)amine, N-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-2-ethylhexyl ether)amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-hexyl ether)amine, N-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-hexyl ether) amine;N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl butyl ether) amine;and N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-neodecanoicester) amine.

Most preferably, the compound is selected from the group consisting ofN,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl butyl ether) amine;N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-2-ethylhexyl ether)amine; N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-tetradecylether) amine; N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-dodecylether) amine; andN,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-neodecanoic ester)amine.

The tertiary alkanolamine compounds can be prepared by reacting aterminal epoxy compound with the corresponding tertiary alkylamine inthe appropriate molar ratios at temperatures from about 50° C. to about250° C., preferably from about 80° C. to about 150° C. (where R⁶represents —CH₂C(R⁷)(OH)CH₂OR⁸).

Since the reaction is exothermic, it is preferable to add the epoxycompound to the tertiary alkylamine at a slow rate (over 1–2 hours)since the heat evolved is derived from opening the epoxy ring. Addingthe tertiary alkylamine to the epoxy compound could produce an unsafesituation where a large exotherm would be generated, particularly in thepresence of a tertiary amine, which catalyzes the opening of the epoxyring.

The tertiary alkanolamine compounds of the present invention can be usedin catalyst compositions to catalyze polyurethane applications, i.e.,the reaction between an isocyanate functionality and an activehydrogen-containing compound, i.e., an alcohol, a polyol, an amine, orwater. The catalyst compositions also catalyze the urethane (gelling)reaction of polyol hydroxyl groups with isocyanate to make polyurethanesand the blowing reaction of water with isocyanate to release carbondioxide for making foamed polyurethanes.

The flexible polyurethane foam products are prepared using any suitableorganic polyisocyanates known in the art including, for example,hexamethylene diisocyanate, phenylene diisocyanate, toluene diisocyanate(TDI) and 4,4′-diphenylmethane diisocyanate (MDI). Especially suitableare the 2,4- and 2,6-TDI's individually or together as theircommercially available mixtures. Other suitable isocyanates are mixturesof diisocyanates known commercially as “crude MDI”, marketed as PAPI byDow Chemicals, which contains about 60% of 4,4′-diphenylmethanediisocyanate along with other isomeric and analogous higherpolyisocyanates. Also suitable are “prepolymers” of thesepolyisocyanates comprising a partially prereacted mixture of apolyisocyanate and a polyether or polyester polyol.

Illustrative examples of suitable polyols as a component of thepolyurethane composition are the polyalkylene ether and polyesterpolyols. The polyalkylene ether polyols include the poly(alkylene oxide)polymers such as poly(ethylene oxide) and poly(propylene oxide) polymersand copolymers with terminal hydroxyl groups derived from polyhydriccompounds, including diols and triols; for example, ethylene glycol,propylene glycol, 1,3-butane diol, 1,4-butane diol, 1,6-hexane diol,neopentyl glycol, diethylene glycol, dipropylene glycol,pentaerythritol, glycerol, diglycerol, trimethylol propane and similarlow molecular weight polyols.

In the practice of this invention, a single high molecular weightpolyether polyol may be used. Also, a mixture of high molecular weightpolyether polyols such as mixtures of di- and tri-functional materialsand/or different molecular weight or different chemical compositionmaterials may be used.

Useful polyester polyols include those produced by reacting adicarboxylic acid with an excess of a diol, for example, adipic acidwith ethylene glycol or butanediol, or reaction of a lactone with anexcess of a diol such as caprolactone with propylene glycol.

In addition to the polyester and polyethers polyols, the master batches,or premix compositions, frequently contain a polymer polyol. Polymerpolyols are used in polyurethane foams to increase the foam's resistanceto deformation, i.e., to increase the load-bearing properties of thefoam. Currently, two different types of polymer polyols are used toachieve load-bearing improvement. The first type, described as a graftpolyol, consists of a triol in which vinyl monomers are graftcopolymerized. Styrene and acrylonitrile are the usual monomers ofchoice. The second type, a polyurea modified polyol, is a polyolcontaining a polyurea dispersion formed by the reaction of a diamine andTDI. Since TDI is used in excess, some of the TDI may react with boththe polyol and polyurea. This second type of polymer polyol has avariant called PIPA polyol, which is formed by the in-situpolymerization of TDI and alkanolamine in the polyol. Depending upon theload-bearing requirements, polymer polyols may comprise 20–80% of thepolyol portion of the master batch.

Other typical agents found in the polyurethane foam formulations includechain extenders such as ethylene glycol and butane diol; cross-linkerssuch as diethanolamine, diisopropanolamine triethanolamine andtripropanolamine; blowing agents such as water, CFCs, HCFCs, HFCs,pentane, and the like; and cell stabilizers such as siliconesurfactants.

A general polyurethane flexible foam formulation according to theinvention would comprise the following components in parts by weight(pbw):

Polyol  20–100 Polymer Polyol 80–0  Silicone Surfactant   1–2.5 Blowingagent   2–4.5 Crosslinker 0.5–2   Catalyst 0.25–2   Isocyanate Index 70–115

The tertiary alkanolamine compounds can be used in conjunction with agelling catalyst, such as a tertiary amine or a suitable transitionmetal catalyst, and/or a blowing catalyst depending upon the processingadvantages desired.

Examples of suitable tertiary amine gelling catalysts include, but arenot restricted to, diazabicyclooctane (triethylenediamine), suppliedcommercially as DABCO 33LV® catalyst by Air Products & Chemicals Inc.,quinuclidine and substituted quinuclidines, substituted pyrrolidines andpyrrolizidines. Examples of suitable tertiary amine blowing catalystsinclude, but are not restricted to, bis-dimethylaminoethyl ether,commercially supplied as DABCO® BL11 catalyst by Air Products andChemicals, Inc., pentamethyl-diethylenetriamine and relatedcompositions, higher permethylated polyamines,2-[N-(dimethylaminoethoxyethyl)-N-methylamino]ethanol and relatedstructures, alkoxylated polyamines, imidazole-boron compositions andamino propyl-bis(aminoethyl)ether compositions.

A catalytically effective amount of the catalyst composition comprisingthe tertiary alkanolamine compound and a tertiary amine gelling orblowing catalyst may be used in the polyurethane formulation. Morespecifically suitable amounts of the catalyst composition may range fromabout 0.01 to 10 parts by wt per 100 parts polyol (pphp) in thepolyurethane formulation, preferably 0.05 to 2 pphp.

The catalyst composition may be used in combination with, or alsocomprise, other tertiary amines, organotin or carboxylate urethanecatalysts well known in the urethane art.

The present invention provides novel tertiary alkanolamines representedby formula (I) prepared by reacting a terminal epoxy compound with aprimary or secondary amine. The present invention also provides a methodfor preparing a polyurethane foam which comprises reacting an organicpolyisocyanate and a polyol in the presence of water as a blowing agent,a cell stabilizer, and a tertiary amine amide catalyst compositionrepresented by formula (I). The present invention further provides theimprovement of enabling the reaction between water and isocyanate tocause blowing of the foam while maintaining and controlling the physicalproperties of the foam which comprises using a tertiary amino alkylamide catalyst composition represented by formula (I).

Although the present invention has been described as useful forpreparing flexible polyurethane foams, the invention may also beemployed to prepare semi-flexible and rigid polyurethane foams. Rigidpolyurethane foams can be distinguished from flexible polyurethane foamsby the presence of higher isocyanurate levels in the rigid foam.Flexible foams typically use polymer polyol as part of the overallpolyol content in the foam composition, along with conventional triolsof 4000–5000 weight average molecular weight (Mw) and hydroxyl number(OH#) of 28–35. In contrast, rigid polyurethane foam compositions use500–1000 Mw polyol with 3–8 hydroxyl functionalities and OH# of 160–700.Rigid foams can also be distinguished from the flexible foams by theisocyanate (NCO) index of the foam composition. Rigid foam compositionstypically use a 100–300 NCO index whereas flexible foam compositionstypically require a 70–115 NCO index.

A general polyurethane rigid insulating foam formulation containing thecatalyst composition according to the invention would comprise thefollowing components in parts by weight (pbw):

Polyol 100 Silicone Surfactant 1–3 Blowing Agent  0–50 Water 0–8Catalyst 0.5–15  Isocyanate Index  80–300

For making lamination (insulation board) and appliance foams the NCOindex is typically 100–300; for making open cell foam the NCO index istypically 100–120 and the foam is usually all water blown.

Semiflexible molded foams have been utilized for many applications inthe automotive area. The major applications are instrument panels andinterior trims. A typical semiflexible foam formulation containing thecatalyst composition according to the invention comprise the followingcomponents in parts by weight (pbw):

SPECFLEX NC 630 Polyol 80.0 SPECFLEX NC 710 20.0 Copolymer Cross-linker1.5 Water 2.2 Catalyst 0.5–10 Black Colorant 0.3 Adhesion Promoter 2.0Cell Opener 1.0 Polymeric MDI, Index 105

The two main components are the base polyol and copolymer polyol (CPP).The base polyol is utilized at levels between 70–100%. The molecularweight of base polyols range from 4500 to 6000 for triols and 2000 to4000 for diols. Ethylene-oxide-capped polyether polyols have replacedmost polyester polyols as the base polyol. The primary hydroxyl contentis usually grater than 75% and the capping range is typically 10–20%.The other major component is CPP, which are used at levels of 0 to 20%.The base polyol and CPP are blended with low molecular weight crosslinkers to build hardness and promote faster demolding. The level ofcross linker varies depending on the hardness requirement of thefinished part. Water levels are chosen to give free rise densities from3 to 6 pounds. Cell openers are also utilized in semiflexible foams toreduce the internal foam pressure during the cure cycle and thus reducepressure-relief voids and “parting lines”. Adhesion promoters can beadded, depending upon the quality of the vinyl skin, to improve theadhesion between the polyurethane foam and the vinyl skin. The use ofthe catalyst composition of the present invention can reduce thediscoloration of the vinyl skin typically observed with conventionalamine catalysts because the hydroxyl group can react with the isocyanateto form a covalent bond with the polyurethane polymer.

Throughout this disclosure, applicant will suggest various theories ormechanisms by which applicant believes the present methods function.While applicant may offer various mechanisms to explain the presentinvention, applicant does not wish to be bound by theory. These theoriesare suggested to better understand the present invention but are notintended to limit the effective scope of the claims.

Throughout this application, various publications have been referenced.The disclosures in these publications are incorporated herein byreference in order to more fully describe the state of the art.

The present invention is further illustrated by the following examples,which are presented for purposes of demonstrating, but not limiting, thepreparation of the compounds and compositions of this invention.

EXAMPLES Example 1 Reaction betweenN,N-bis-(3-dimethylaminopropyl)-amine (Polycat®-15) and butyl glycidylether (EPODIL® 741) to YieldN,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl butyl ether) amine

N,N-bis-(3-dimethylaminopropyl)-amine (54.3 g, 0.29 mol) was placed intoa 500 ml three necked round bottom flask equipped with a Teflon® coatedmagnetic stir bar and a pressure equalizing dropping funnel. The aminewas heated to 80° C. under nitrogen and butyl glycidyl ether (45 g, 0.29mol) was slowly added over a period of 30 minutes. A mild exotherm wasobserved during the addition that caused the temperature to rise toabout 84° C. At the end of the addition, the liquid was heated to 120°C. and maintained at that temperature for about 30 minutes yielding99.29 g of product.

Example 2 Reaction between N,N-bis-(3-dimethylaminopropyl)-amine(Polycat®-15) and 2-ethylhexyl glycidyl ether (EPODIL® 746) to YieldN,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-2-ethylhexyl ether)amine

N,N-bis-(3-dimethylaminopropyl)-amine (52.8 g, 0.28 mol) was placed intoa 500 ml three necked round bottom flask equipped with a Teflon® coatedmagnetic stir bar and a pressure equalizing dropping funnel. The aminewas heated to 80° C. under nitrogen and 2-ethylhexyl glycidyl ether (50g, 0.29 mol) was slowly added over a period of 30 minutes. A mildexotherm was observed during the addition that caused the temperature torise to about 88° C. At the end of the addition, the liquid was heatedto 120° C. and maintained at that temperature for about 30 minutesyielding 102.8 g of product.

Example 3 Reaction between N,N-bis-(3-dimethylaminopropyl)-amine(Polycat®-15) and Alkyl (C12–C14) glycidyl ether (EPODIL® 748) to YieldN,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-tetradecyl ether)amine and N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-dodecylether) amine

N,N-bis-(3-dimethylaminopropyl)-amine (51.9 g, 0.28 mol) was placed intoa 500 ml three necked round bottom flask equipped with a Teflon® coatedmagnetic stir bar and a pressure equalizing dropping funnel. The aminewas heated to 80° C. under nitrogen and alkyl (C12–C14) glycidyl ether(75 g, 0.28 mol) was slowly added over a period of 30 minutes. A mildexotherm was observed during the addition that caused the temperature torise to about 84° C. At the end of the addition, the liquid was heatedto 120° C. and maintained at that temperature for about 30 minutesyielding 126.9 g of product.

Example 4 Reaction between N,N-bis-(3-dimethylaminopropyl)-amine(Polycat®-15) and Cardura®E-10 to YieldN,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-neodecanoic ester)amine

N,N-bis-(3-dimethylaminopropyl)-amine (52.36 g, 0.28 mol) was placedinto a 500 ml three necked round bottom flask equipped with a Teflon®coated magnetic stir bar and a pressure equalizing dropping funnel. Theamine was heated to 80° C. under nitrogen and Cardura®E-10 (70 g, 0.28mol) was slowly added over a period of 30 minutes. A mild exotherm wasobserved during the addition that caused the temperature to rise toabout 84° C. At the end of the addition, the liquid was heated to 120°C. and maintained at that temperature for about 30 minutes yielding126.9 g of product. Cardura®E-10 is a commercially available gycidylester of Versatic acid. It is a synthetic, saturated monocarboxylic acidmixture of highly branched C10 isomers. The structure where at least oneof the alkyl groups is a methyl.

Example 5 Rate of Rise of Foams Made with Different Polycat®-15/EPODIL®Adducts

In this example, polyurethane foams were prepared in a conventionalmanner. The polyurethane formulation in parts by weight was:

COMPONENT PARTS ARCOL E848¹ 50.00 ARCOL E851² 50.00 WATER 2.34 DABCO ®DC 5043³ 0.75 DEOA-LF⁴ 1.76 DABCO 33LV ®⁵ 0.25 DABCO ® BL-11⁶ 0.10 TDI30.25 Index 100 ^(1–2)commercially available polyols; ³commercialsilicon surfactant supplied by Air Products & Chemicals; ⁴Cross-linker;⁵DABCO 33LV ® is a commercially available catalysts supplied by AirProducts & Chemicals (33% solution of triethylenediamine in dipropyleneglycol); ⁶DABCO ® BL-11 is a commercially available catalyst supplied byAir Products & Chemicals (70% solution of bis-dimethylaminoethylether indipropylene glycol)

For each foam, the catalyst was added to 158 g of the above premix in a32 oz (951 ml) paper cup and the formulation was mixed for 10 sec at6,000 RPM using an overhead stirrer fitted with a 2 in (5.1 cm) diameterstirring paddle. Sufficient TDI 80 was added to make a 100 index foam[index=(mole NCO/mole of active hydrogen)×100] and the formulation wasmixed well for 6 sec at 6,000 RPM using the same stirrer. The 32 oz cupwas dropped through a hole in the bottom of a 128 oz (3804 ml) paper cupon a stand. The hole was sized to catch the lip of the 32 oz cup. Thetotal volume of the foam container was 160 oz (4755 ml). Foamsapproximated this volume at the end of the foam forming process. Maximumfoam height was recorded.

POLYCAT ® POLYCAT ® POLYCAT ® PC-15 PC-15 PC-15 Run DABCO DABCO ®DABCO ® TEXACAT ® and and and # 33LV ® BL-11 NE1060¹ ZF-10²Epodil ® 748³ Epodil ® 746⁴ Epodil ® 741⁵ 1 0.25 0.1 2 0.56 0.16 3 0.700.50 4 0.70 0.50 5 0.79 0.50 Run # Cream Cup1 String Gel Full Rise 18.40 16.70 65.30 100.1  2 8.10 14.90 69.90 96.40 3 8.70 15.70 66.2087.40 4 8.30 15.70 — 94.80 5 8.20 15.50 64.60 83.90 ¹DABCO ® NE1060 is acommercially available catalyst supplied by Air Products & Chemicals.The catalysts is a 75% dipropylene glycol solution ofN-(3-dimethylaminopropyl)-urea (87%) and N,N′-bis-(3-dimethylamino)-urea(13%); ²TEXACAT ® ZF-10 is a commercially available catalysts based on2-[N-(dimethylaminoethoxyethyl)-N-methylamino]ethanol; ³Epodil ® 748 isa commercially available epoxy product supplied by Air Products &Chemicals. The product is mainly composed of alkyl (C12–C14) glycidylether; ⁴Epodil ® 746 is a commercially available epoxy product suppliedby Air Products & Chemicals. The product is mainly composed of2-ethyl-hexyl glycidyl ether; ⁵Epodil ® 741 is a commercially availableepoxy product supplied by Air Products & Chemicals. The product ismainly composed of butyl glycidyl ether.

DABCO 33LV ® /- POLYCAT ® 15 POLYCAT ® 15 POLYCAT ® 15 DABCO ® - and andand PARAMETER BL-11 Epodil ® 748 Epodil ® 746 Epodil ® 741 PPHP 0.120.20 0.20 0.20 MOLES* × 10³ 0.80 0.90 1.08 1.26 MOLECULAR WEIGHT —429–457 373 317 MIXING TIME [s] 12 12 12 12 TEST TIME [s] 300 300 300300 RISE HEIGHT [mm] 258.4 259.4 263.4 258.9 RISE TIME [s] 130.4 139.2160.3 137.1 MAX HEIGHT [mm] 263.7 264.7 268.8 264.1 FINAL HEIGHT [mm]263.0 263.6 267.2 262.6 SHRINKAGE [%] 0.3 0.4 0.6 0.7 *moles ofcatalytically active nitrogen

The data shows a good rate match between the industry standard (DABCO33LV®/DABCO®BL-11) and the different Polycar®-15/Epodil adducts. Mostsurprisingly, the data shows that the same catalyst usage is requiredfor all Polycat®-15/EPODIL® adducts even though there is a substantialdifference in their sizes and molecular weights. Thus, the Me₂N— groupsare presumably more active in the Polycat®-15/EPODIL®748 than in theother adducts.

Under these circumstances, the highest molecular weight catalysts hasthe advantage that amine emissions in finish products are going to begreatly reduced. Thus, the low vapor pressure, the low odor, thepresence of a secondary hydroxyl group capable of immobilizing the amineduring/after polymerization and the lower concentration of amine inPolycat®-15/EPODIL®748 adduct are some of the advantages offer by thisnew product.

Example 6 Rate of Rise of Foams Made with Polycat®15-Epodil® 748 Adducts

The following data provides a comparison between DABCO®BLV (industrystandard) and the Polycat®15-EPODIL® 748 adducts prepared according tothe procedures of example 4 and 5.

Polycat ® 15- Polycat ® 15- Polycat ®15- EPODIL ® 748 EPODIL ® 748EPODIL ® 748 FROM FROM FROM PARAMETER DABCO ® BLV Example 4 Example 5Example 5 PPHP 0.12 0.80 1.40 1.60 MOLES* × 10³ 0.80 2.0 2.0 2.0 MIXINGTIME [s] 12 12 12 12 TEST TIME [s] 300 300 300 300 RISE HEIGHT 294.8307.2 308.3 302.8 [mm] RISE TIME [s] 104.5 128.6 124.9 103.3 MAX HEIGHT300.6 313.2 314.3 308.6 [mm] FINAL HEIGHT 299.3 311.0 312.6 306.6 [mm]*moles of catalytically active nitrogen

Good kinetic match was obtained with both Polycat®15 derivativesrequiring relatively modest catalyst loadings when the Polycat®15/alkyl(C12–C14) glycidyl ether mono-adduct prepared in example 4 was used. Theexample shows that the catalytic activity of the M₂N— group did notincrease in going from the mono- to the bis-adduct because the samenumber of moles were required to obtain rate match.

Example 7 Comparison between the Physical Properties of Foams Made withDabco®BLV Industry Standard and with Polycat®15-Epodil® 748 Adduct

This example provides a comparison between the physical properties offoams made with BLV (industry standard) and DMAPA-EPODIL®748. Largerfoams (scale factor=3.2) were prepared using the following formulation:

COMPONENT PARTS VORANOL 3512A¹ 100.00 WATER 4.60 DABCO ® DC 5982² 0.90AMINE CATALYST³ VARIABLE DABCO ® T-10⁴ VARIABLE: 0.52–0.32 TDI 56.20Index 108 ¹polyol; ²commercial silicon surfactant supplied by AirProducts & Chemicals; ³Standard is DABCO ® BLV, a commercially availablecatalysts supplied by Air Products & Chemicals composed of 75 wt. % ofDABCO 33LV ® (a 33% solution of triethylenediamine in dipropyleneglycol) and 25 wt. % of DABCO ® BL-11 (70% solution ofbis-dimethylaminoethylether in dipropylene glycol); ⁴a commerciallyavailable tin catalyst supplied by Air Products & Chemicals.

For each foam, the catalyst was added to 339.2 g of the above premix ina 32 oz (951 ml) paper cup and the formulation was mixed for 10 sec at6,000 RPM using an overhead stirrer fitted with a 2 in (5.1 cm) diameterstirring paddle. Sufficient TDI 80 was added to make a 108 index foam[index=(mole NCO/mole of active hydrogen)×100] and the formulation wasmixed well for 6 sec at 6,000 RPM using the same stirrer. The contentwas poured into a 3.5 gallon container. Foams approximated this volumeat the end of the foam forming process. Maximum foam height was recordedand the physical properties evaluated. In the case of air flows anddensities, the foams were cut in three sections of equal length top,middle and bottom and the these properties were measured on each sectionto compare air flow and density distribution across the length of thefoam.

DABCO ® T-10 LEVEL: 0.52 PPHP Average Average Tear Tensile Average AirFlow Density Strength Stength Break Catalyst (SCFM) (lb/scft) (lbf)(psi) Elongation % DABCO ® Top: Top: 2.19 ± 0.26 11.56 ± 0.37 137.25 ±4.15  BLV 2.96 ± 0.16 1.278 ± 0.032 Middle: Middle: 2.43 ± 0.01 1.346 ±0.01  Bottom: Bottom: 1.36 ± 0.16 1.521 ± 0.053 Polycat ® 15/ Top: Top:2.17 ± 0.20 11.23 ± 0.69 129.98 ± 22.99 EPODIL ® 748 3.26 ± 0.08 1.295 ±0.024 Middle: Middle: 2.50 ± 0.20 1.366 ± 0.019 Bottom: Bottom: 1.19 ±0.03 1.525 ± 0.005

DABCO ® T-10 LEVEL: 0.42 PPHP Average Average Tear Tensile Average AirFlow Density Strength Stength Break Catalyst (SCFM) (lb/scft) (lbf)(psi) Elongation % DABCO ® Top: Top: 2.07 ± 0.10 10.22 ± 0.30 117.56 ±9.49 BLV 4.20 ± 0.01 1.308 ± 0.015 Middle: Middle: 3.57 ± 0.48 1.358 ±0.025 Bottom: Bottom: 2.66 ± 0.47 1.554 ± 0.008 Polycat15 ®/ Top: Top:1.97 ± 0.23 10.05 ± 0.38 119.42 ± 7.64 EPODIL ® 748 4.62 ± 0.12 1.297 ±0.02  Middle: Middle: 4.02 ± 0.23 1.371 ± 0.019 Bottom: Bottom: 2.84 ±0.06 1.503 ± 0.001

DABCO ® T-10 LEVEL: 0.32 PPHP Average Average Tear Tensile Average AirFlow Density Strength Stength Break Catalyst (SCFM) (lb/scft) (lbf)(psi) Elongation % DABCO ® Top: Top: 2.00 ± 0.19 9.75 ± 0.33 116.94 ±8.43  BLV 5.46 ± 0.19 1.324 ± 0.004 Middle: Middle: 5.05 ± 0.01 1.377 ±0.017 Bottom: Bottom: 3.73 ± 0.07 1.545 ± 0.014 Polycat15 ®/ Top: Top:1.95 ± 0.12 10.87 ± 1.02 135.70 ± 23.06 EPODIL ® 748  6.0 ± 0.05 1.297 ±0.002 Middle: Middle: 5.64 ± 0.25 1.296 ± 0.003 Bottom: Bottom: 4.84 ±0.12 1.422 ± 0.012

Thus, the physical properties of the foams made with DABCO®BLV andPolycat®15/EPODIL®748 are very similar. At lower tin levels,Polycat®15/EPODIL®748 seem to provide foams with better air flows thanthe standard without sacrificing tear and tensile strength.

Example 8 Dynamic Surface Tension of Aqueous Solutions ContainingDifferent Polycat®15/Epodil® Adducts

In this example, the different Polycat®15/EPODIL® adducts were dissolvedin water and the dynamic surface tension were measured. The data issummarized below showing a comparison among the differentPolycat®15/Epodil® adducts.

10.0 20.0 Additive-Amount wt. % 0.1 b/s 1.0 b/s 6.0 b/s b/s b/sPolycat ® 15/Epodil ® 741- 42.7 46.7 48.9 49.9 50.9 0.1 wt. % Polycat ®15/Epodil ® 741- 39.9 43.9 46.7 47.5 49.5 0.3 wt. % Polycat ®15/Epodil ® 746- 30.0 36.0 39.4 41.5 43.5 0.1 wt. % Polycat ®15/Epodil ® 748- 31.9 32.9 36.2 36.9 37.4 0.1 wt. % Polycat ®15/Cardura ® 32.4 36.0 39.3 40.8 42.1 E10-0.1 wt. %

While a number of embodiments of this invention have been represented,it is apparent that the basic construction can be altered to provideother embodiments which utilize the invention without departing from thespirit and scope of the invention. All such modifications and variationsare intended to be included within the scope of the invention as definedin the appended claims rather than the specific embodiments which havebeen presented by way of example.

1. A compound represented by formula (I):

wherein A represents CH or N; R¹ represents

 and R⁶ represents —CH₂C(R⁷)(OH)CH₂OR⁸; or R¹ represents—CH₂C(R⁷)(OH)CH₂OR⁸ and R⁶ represents an alkyl or alkenyl group havingC₄–C₃₆ carbon atoms; or R¹ represents

 and R⁶ represents —CH₂C(R⁷)(OH)R⁸; or R¹ represents —CH₂C(R⁷)(OH)R⁸ andR⁶ represents an alkyl or alkenyl group having C₄–C₃₆ carbon atoms; R²and R³ each represent hydrogen or an alkyl or alkenyl group having C₁–C₆carbon atoms; R⁴ and R⁵ each represent an alkyl group having C₁–C₆carbon atoms when A represents N; or R⁴ and R⁵ together represent aC₂–C₅ alkylene group when A represents N; or R⁴ and R⁵ togetherrepresent a C₂–C₅ alkylene group containing NR¹⁰ or NR¹¹ when A is CH orN, where R¹⁰ is hydrogen or an alkyl group having C₁–C₄ carbon atoms andR¹¹ is an alkyl group having C₁–C₄ carbon atoms or

R⁷ represents hydrogen or an alkyl or alkenyl group having C₁–C₅ carbonatoms; R⁸ represents an alkyl or alkenyl group having C₄–C₃₆ carbonatoms or —COR⁹, where R⁹ represents an alkyl or alkenyl group havingC₃–C₃₅ carbon atoms; and n is an integer from 1 to
 3. 2. The compound ofclaim 1, wherein R¹ is


3. The compound of claim 1, wherein R² and R³ are hydrogen.
 4. Thecompound of claim 1, wherein R⁴ and R⁵ are alkyl groups having C₁–C₆carbon atoms when A represents N.
 5. The compound of claim 1, wherein R⁴and R⁵ together represent —CH₂CH₂N(CH₃)CH₂—.
 6. The compound of claim 1,wherein R⁷ is hydrogen.
 7. The compound of claim 1, wherein R⁸ is analkyl or alkenyl group having C₄–C₂₂ carbon atoms or —COR⁹.
 8. Thecompound of claim 1, wherein R⁹ is an alkyl or alkenyl group havingC₃–C₂₂ carbon atoms.
 9. The compound of claim 1, wherein n is 2 or 3.10. The compound of claim 1, wherein the compound is selected from thegroup consisting ofN,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-octadecyl ether)amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-hexadecylether) amine,N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-tetradecyl ether)amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-dodecyl ether)amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-decyl ether)amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-octyl ether)amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-2-ethylhexylether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-hexylether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hexanol) amine,N-(3-dimethylaminopropyl)-N-(2-hexanol) amine,N,N-bis-(3-dimethylaminopropyl)-N-(2-octanol) amine,N-(3-dimethylaminopropyl)-N-(2-octanol) amine,N,N-bis-(3-dimethylaminopropyl)-N-(2-decanol) amine,N-(3-dimethylaminopropyl)-N-(2-decanol) amine,N,N-bis-(3-dimethylaminopropyl)-N-(2-dodecanol) amine,N-(3-dimethylaminopropyl)-N-(2-dodecanol) amine,N,N-bis-(3-dimethylaminopropyl)-N-(2-tetradecanol) amine,N-(3-dimethylaminopropyl)-N-(2-tetradecanol) amine,N,N-bis-(3-dimethylaminopropyl)-N-(2-hexadecanol) amine,N-(3-dimethylaminopropyl)-N-(2-hexadecanol) amine,N,N-bis-(3-dimethylaminopropyl)-N-(2-octadecanol) amine,N-(3-dimethylaminopropyl)-N-(2-octadecanol) amine;N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl butyl ether) amine;and N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-neodecanoicester) amine.
 11. The compound of claim 10, wherein the compound isselected from the group consisting ofN,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-octadecyl ether)amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-hexadecylether) amine,N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-tetradecyl ether)amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-dodecyl ether)amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-decyl ether)amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-octyl ether)amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-2-ethylhexylether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-hexylether) amine, N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl butylether) amine; andN,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-neodecanoic ester)amine.
 12. The compound of claim 11, wherein the compound isN,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl butyl ether) amine.13. The compound of claim 11, wherein the compound isN,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-2-ethylhexyl ether)amine.
 14. The compound of claim 11, wherein the compound isN,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-tetradecyl ether)amine.
 15. The compound of claim 11, wherein the compound isN,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-dodecyl ether) amine.16. The compound of claim 11, wherein the compound isN,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-neodecanoic ester)amine.
 17. The compound of claim 11, wherein the compound is a mixtureof N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-tetradecyl ether)amine and N,N-bis-(3-dimethylaminopropyl)-N-(2-hydroxypropyl-dodecylether) amine.